CH143617A - Process for the preparation of a guanidine derivative. - Google Patents
Process for the preparation of a guanidine derivative.Info
- Publication number
- CH143617A CH143617A CH143617DA CH143617A CH 143617 A CH143617 A CH 143617A CH 143617D A CH143617D A CH 143617DA CH 143617 A CH143617 A CH 143617A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- tetrahydroquinaldine
- reaction
- guanidine derivative
- chlorohydrate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002357 guanidines Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- JZICUKPOZUKZLL-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(C)CCC2=C1 JZICUKPOZUKZLL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- -1 tetrahydroquinaldine chlorohydrate forms Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Guanidinderivates. Es wurde gefunden, dass man zu einem Guanidinderivat gelangen kann, indem man Tetrahydroehinaldin, zweckmässig in Gegen wart eines Lösungsmittels, mit Cyanamid umsetzt. Es kann bei der Ausführung des Verfahrens auch von Salzen des Tetrahydro- chinaldins und Cyanamids ausgegangen wer den.
Das Guanyl-tetrahydrochinaldin-chlorhy- drat bildet glasklare Prismen vom Schmelz punkt 184-1 & 5 . Sowohl das Chlorhydrat, wie die freie Base sind in Wasser löslich, ,jenes mit neutraler, dieses mit stark alka lischer Reaktion.
Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> 147 Teile Tetrahydrochinaldin werden in 500 Teilen Alkohol gelöst, mit alkoholischer Salzsäure neutralisiert und nach Zusatz von 60 Teilen Cyanamid einige Stunden auf 150 bis 160 erhitzt. Das Reaktionsprodukt wird vom Alkohol befreit, in etwas Wasser gelöst und mit Kaliumkarbonatlösung versetzt. Die ausgefallene Basenschicht wird abgetrennt. mit Äther ausgeschüttelt und in einer Mi schung von Essigester und absolutem Alko hol gelöst. Nach dem Trocknen mit Kalium karbonat wird mit alkoholischer Salzsäure neutralisiert.
Das nach dem Verdampfen des Lösungsmittels zurückbleibende 01 wird in einer Mischung von Aceton und absolutem Alkohol gelöst, wobei das Chlorhydrat des Guanyl - tetrahydrochinaldins auskristalli siert.
An Stelle von Äthylalkohol können für die Umsetzung andere Lösungsmittel, zum Beispiel Methylalkohol oder Wasser, verwen det werden.
Process for the preparation of a guanidine derivative. It has been found that a guanidine derivative can be obtained by reacting tetrahydroehinaldine, advantageously in the presence of a solvent, with cyanamide. When carrying out the process, it is also possible to start from salts of tetrahydroquinaldine and cyanamide.
The guanyl tetrahydroquinaldine chlorohydrate forms crystal-clear prisms with a melting point of 184-1 & 5. Both the chlorohydrate and the free base are soluble in water, the one with a neutral reaction, the other with a strongly alkaline reaction.
The new compound should find therapeutic use.
<I> Example: </I> 147 parts of tetrahydroquinaldine are dissolved in 500 parts of alcohol, neutralized with alcoholic hydrochloric acid and, after addition of 60 parts of cyanamide, heated to 150 to 160 for a few hours. The reaction product is freed from alcohol, dissolved in a little water and treated with potassium carbonate solution. The precipitated base layer is separated off. shaken out with ether and dissolved in a mixture of ethyl acetate and absolute alcohol. After drying with potassium carbonate, it is neutralized with alcoholic hydrochloric acid.
The oil that remains after the solvent has evaporated is dissolved in a mixture of acetone and absolute alcohol, the guanyl-tetrahydroquinaldine hydrochloride crystallizing out.
Instead of ethyl alcohol, other solvents, for example methyl alcohol or water, can be used for the reaction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143617T | 1928-07-24 | ||
| CH537302X | 1928-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143617A true CH143617A (en) | 1930-11-15 |
Family
ID=25714299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143617D CH143617A (en) | 1928-07-24 | 1928-07-24 | Process for the preparation of a guanidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143617A (en) |
-
1928
- 1928-07-24 CH CH143617D patent/CH143617A/en unknown
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